Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives

Timonen, Juri M.; Nieminen, Riina; Sareila, Outi; Goulas, A.; Moilanen, Lauri J.; Haukka, Matti; Vainiotalo, Pirjo; Moilanen, Eeva; Aulaskari, Paula

doi:10.1016/j.ejmech.2011.05.052

Cited by 98 publications

(54 citation statements)

References 9 publications

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“…The introduction of electron‐donating groups into coumarin will further improve the fluorescence performance of coumarin derivatives through intermolecular electron transfer . It has also been reported that a few of the coumarin derivatives can offer antibacterial, anticarcinogenic, and analgesic activity and that they also serve as antioxidant and anti‐inflammatory agents, and as HIV protease inhibitors . Coumarins and their derivatives can be synthesized by several routes, including the Pechmann, Perkin, Knoevenagel, Reformatsky, and Wittig reactions by using acidic or basic catalysts.…”

Section: Introductionmentioning

confidence: 99%

Preparation of Highly Active Triflic Acid Functionalized SBA‐15 Catalysts for the Synthesis of Coumarin under Solvent‐Free Conditions

et al. 2015

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Highly acidic SBA‐15 with different pore diameters has been prepared by functionalizing the mesoporous walls with different amounts of triflic acid (TFA). The structure of the SBA‐15 before and after the functionalization with TFA was investigated by powder X‐ray diffraction and nitrogen adsorption isotherms. The interaction of TFA with the surface silanol groups of SBA‐15 and the acidity of the materials have been investigated by FTIR spectroscopy and temperature‐programmed desorption of ammonia, respectively. The characterization results reveal that the mesoporous structure of the SBA‐15 is retained even after the loading of TFA in the mesochannels and that the TFA molecules are bonded with the surface silanol groups of the SBA‐15 supports. The acidity of the materials increases with increasing amount of TFA from 5 to 20 wt %. These functionalized, highly acidic materials are found to be highly active in the synthesis of coumarin and the catalytic efficiency was found to correlate with the total acidity or the amount of TFA in the porous channels of the SBA‐15 catalysts. It has also been found that the activity of the TFA‐functionalized SBA‐15 in the synthesis of coumarin is much higher than that of different zeolites, pure mesoporous silica SBA‐15, and other mesoporous catalysts used in this study.

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Section: Introductionmentioning

confidence: 99%

Preparation of Highly Active Triflic Acid Functionalized SBA‐15 Catalysts for the Synthesis of Coumarin under Solvent‐Free Conditions

et al. 2015

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“…The second step of the synthesis was the Pechmann reaction, commonly used for the synthesis of coumarins [42,43]. Methyl 2-fluorobenzoylacetate (3) was reacted with resorcinol (4) in the presence of H 2 SO 4 at 35 °C, and 7-hydroxy-4-(2-fluorophenyl)coumarin (5) [39,44] was obtained as a light yellow solid. The last step of the synthesis was the methylation of the hydroxy group of coumarin 5 with dimethyl sulfate, to form 4-(2-fluorophenyl)-7-methoxycoumarin (6).…”

Section: Resultsmentioning

confidence: 99%

“…Splitting of the H5 signal was observed in both solvents ( Figure 1) suggesting that the 19 F-H5 coupling for coumarin 6 is solvent independent. A literature report of the NMR characterization of a structurally similar 7-hydroxycoumarin performed in DMSO-d 6 has the signal for H5 reported as a singlet [44].…”

Section: Discussionmentioning

confidence: 99%

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

Mzozoyana¹,

Heerden²,

Grimmer³

2020

Beilstein J. Org. Chem.

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4-(2-Fluorophenyl)-7-methoxycoumarin (6) was synthesized by Pechmann reaction under mild conditions via a three-step reaction. The solution-state 1 H NMR spectra of 6 showed a strong intramolecular interaction between F and H5 (J FH = 2.6 Hz) and 13 C NMR suggested that this C-F···H-C coupling is a through-space interaction. The 2D 19 F-{ 1 H} HOESY and 1 H-{ 19 F} 1D experiments were done to confirm this F···H interaction. The single crystal X-ray structure and the DFT-optimized structure showed that the fluorinated phenyl ring favors the orientation with the fluorine atom closer to H5 than H3. The X-ray structure also showed the existence of the intermolecular C-F···H-C interaction.190

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“…Coumarins (2H-1-benzopyran-2-ones) are well known aromatic δ-lactones isolated from variety of plant sources 1 .Coumarins have a wide range of applications in the field of pharmaceuticals due to their diverse pharmacological and biological propertiessuch as antimicrobial 2 , anticoagulant 3 , antitumor inflammatory 5 , anti-HIV 6 , anticonvulsant antidiabetic 8 , analgesic 9 , antianxiety 10 Coumarins, dicoumarins,krohnke synthesis, antimicrobial screening, broth dilution ones) are well known lactones isolated from variety of plant .Coumarins have a wide range of applications in the field of pharmaceuticals due to their diverse pharmacological and biological propertiessuch as , antitumor 4 , anti-, anticonvulsant 7 , 10 etc.A wide number ofcoumarin derivatives have been found in literature which contain nucleus like pyridine, indole, imidazole, diazole, thiazole, and triazole etc. as a substituent group possess important biological activities [11][12][13][14][15] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and In Vitro Antimicrobial Screening of Some PyrazolylPyridyl Substituted Dicoumarins

Brahmbhatt¹,

Gohil²

2018

IJTSRD

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Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives

Cited by 98 publications

References 9 publications

Preparation of Highly Active Triflic Acid Functionalized SBA‐15 Catalysts for the Synthesis of Coumarin under Solvent‐Free Conditions

Preparation of Highly Active Triflic Acid Functionalized SBA‐15 Catalysts for the Synthesis of Coumarin under Solvent‐Free Conditions

Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds

Synthesis, Characterization and In Vitro Antimicrobial Screening of Some PyrazolylPyridyl Substituted Dicoumarins

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